US4788312A - Trisilahydrocarbon lubricants - Google Patents
Trisilahydrocarbon lubricants Download PDFInfo
- Publication number
- US4788312A US4788312A US07/169,225 US16922588A US4788312A US 4788312 A US4788312 A US 4788312A US 16922588 A US16922588 A US 16922588A US 4788312 A US4788312 A US 4788312A
- Authority
- US
- United States
- Prior art keywords
- sub
- carbon atoms
- bis
- trisilahydrocarbon
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000314 lubricant Substances 0.000 title claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000000543 intermediate Substances 0.000 claims abstract description 13
- 150000001993 dienes Chemical class 0.000 claims abstract description 9
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 8
- 150000001336 alkenes Chemical class 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000005353 silylalkyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000003708 ampul Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000007792 addition Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JNKDFMVKDQOCIL-UHFFFAOYSA-N trichloro-[8-[dichloro(8-trichlorosilyloctyl)silyl]octyl]silane Chemical compound Cl[Si](Cl)(Cl)CCCCCCCC[Si](Cl)(Cl)CCCCCCCC[Si](Cl)(Cl)Cl JNKDFMVKDQOCIL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VRPRVZOWRSROFI-UHFFFAOYSA-N dichloro-bis(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](Cl)(Cl)C=CCCCCCC VRPRVZOWRSROFI-UHFFFAOYSA-N 0.000 description 2
- ZMKPQUDGWYMHCC-UHFFFAOYSA-N dimethyl-bis(8-trimethylsilyloctyl)silane Chemical compound C[Si](C)(C)CCCCCCCC[Si](C)(C)CCCCCCCC[Si](C)(C)C ZMKPQUDGWYMHCC-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical compound [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 description 1
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XMIJDTGORVPYLW-UHFFFAOYSA-N [SiH2] Chemical compound [SiH2] XMIJDTGORVPYLW-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000013520 petroleum-based product Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/76—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing silicon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to synthetic lubricant base stocks based on silane chemistry and to chemical intermediates useful in their preparation. More particularly, it relates to a novel family of trisilahydrocarbons prepared from di halo silane, diolefins, trihalo- and trialkylsilanes, and organometallic and hydridometallic compounds through novel alkenylhalosilane intermediates.
- R', R", and R'" are alkyl groups having from six to twelve carbon atoms.
- These monosilahydrocarbons are described, for example, in C. E. Snyder et al., ASLE Transactions, vol. 25, No. 3, pp. 298-308 (1982).
- These monosilahydrocarbons have been shown to be superior to synthetic hydrocarbons such as the polyalphaolefins in viscosity-temperature properties, oxidative stability, and especially thermal stability, while additionally having advantages over silicones (polysiloxanes) in lubricity and bulk modulus. It is evident that incorporation of the silicon atom into the hydrocarbon skeleton can improve the utility of the structure for synthetic lubricant purposes.
- silahydrocarbons which retain desirable characteristics of the monosilahydrocarbons of the prior art, but which could be prepared in a wider range of molecular weights, viscosities, and volatilities, so as to be suitable not only for the lower-viscosity applications currently satisfied by the prior art materials but for the high-viscosity low-volatility applications as well. It would be further desirable if this new class of silahydrocarbons could be prepared from readily accessible raw materials. It would be additionally desirable to have available relatively simple silicon-containing chemical intermediates, which by the proper choice of reagents could be converted into numerous silahydrocarbon structures designed to have properties suitable for specific applications. Our invention satisfies all of these objects.
- trisilahydrocarbons of our invention we are not aware of the use of trisilahydrocarbons of our invention in synthetic lubricant applications. These trisilahydrocarbons and the chemical intermediates employed in their preparation and disclosed herein are, to the best of our knowledge, new chemical compounds previously unknown.
- R 1 , R 2 , R 3 , R 4 , and R 5 represent alkyl groups having from one to twelve carbon atoms and --A-- represents an alkylene group having from four to sixteen carbon atoms. It is preferable that the alkyl and alkylene groups be unbranched--that is, --A-- is preferably --(CH 2 ) n -- wherein n is from four to sixteen, and R 1 , R 2 , etc. are methyl, ethyl, n-propyl, n-butyl, and so on up to n-dodecyl.
- R 1 , R 2 , etc. may be the same or different alkyl groups, and --A-- is considered to include mixtures of alkylene groups having different chain lengths within the four- to sixteen- carbon range.
- trisilahydrocarbon lubricant base stocks of our invention are prepared by the following steps:
- n is from four to sixteen as above.
- This addition is carried out in the presence of a catalyst, such as hexachloroplatinic acid.
- a catalyst such as hexachloroplatinic acid.
- a considerable excess of diolefin is employed in order to insure that only one of the two double bonds is reacted.
- the unreacted diolefin is subsequently recovered by distillation for further use.
- Y represents halogen, preferably chlorine or bromine, if a trihalosilane is used, or alternatively an alkyl group or mixed alkyl groups having from one to twelve carbon atoms if a trialkylsilane was used.
- Addition of the trihalo- and trialkylsilanes to double bond compounds are carried out in the presence of catalysts, as in the condensation reaction of Step (a) hereinabove.
- Step (c) Replacement of the halogen atoms in the intermediates of Step (b) with alkyl groups by treatment with organometallic compounds of suitable reactivity.
- the alkyl groups will contain from one to twelve carbon atoms.
- Suitable organometallic compounds include the alkyllithium compounds, alkylmagnesium halides (Grignard reagents), alkylsodium compounds, dialkylzinc compounds, and the like, with the alkyllithium compounds and the Grignard reagents being especially preferred.
- Mixtures of organometallic compounds can be employed (for example methyllithium plus n-butyllithium) to achieve mixed alkyl substitution in the final trisilahydrocarbon products.
- the halogen atoms can be replaced by hydrogen by treatment with hydridometallic reducing agents such as lithium aluminum hydride.
- the resulting --Si--H compounds can then be added to olefins in the presence of a suitable catalyst such as platinum acetylacetonate to form the final alkylsilicon products.
- a suitable catalyst such as platinum acetylacetonate
- the use of the organometallic compounds is considered preferable in order to avoid the two-step reaction sequence required by the alternative route. In either case, however, Step (c) results in the formation of a trisilahydrocarbon of our invention having the general formula R 1 R 2 --Si[--A--Si(R 3 R 4 R 5 )] 2 .
- Step (a) and (b) can be prepared in bulk and used to prepare a wide range of trisilahydrocarbons by a suitable choice of organometallic compounds in Step (c).
- the trisilahydrocarbons of our invention as a class of synthetic lubricant, have the advantage of versatility, and can be "tailored” to achieve a wide range of lubricant properties.
- trisilahydrocarbon synthetic lubricant base stocks can be used as prepared; or alternately, they can be formulated with additives designed to impart additional desirable properties appropriate to the application--for example, antioxidants, corrosion inhibitors, antiwear agents, detergents, antifoam agents, and the like.
- additives designed to impart additional desirable properties appropriate to the application--for example, antioxidants, corrosion inhibitors, antiwear agents, detergents, antifoam agents, and the like.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
Abstract
Description
CH.sub.3 --Si (R'R"R'")
R.sub.1 R.sub.2 --Si[--A--Si(R.sub.3 R.sub.4 R.sub.5) ].sub.2
X.sub.2 SiH.sub.2 +2H.sub.2 C═CH--(CH.sub.2).sub.n-4 --CH═CH.sub.2 →[H.sub.2 C═CH--(CH.sub.2).sub.n-4 --CH.sub.2 CH.sub.2 ].sub.2 SiX.sub.2,
[Y.sub.3 Si--CH.sub.2 --CH.sub.2 --(CH.sub.2).sub.n-4 --CH.sub.2 CH.sub.2 ].sub.2 SiX.sub.2,
Claims (5)
R.sub.1 R.sub.2 --Si[--A--Si(R.sub.3 R.sub.4 R.sub.5)].sub.2
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/169,225 US4788312A (en) | 1988-03-16 | 1988-03-16 | Trisilahydrocarbon lubricants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/169,225 US4788312A (en) | 1988-03-16 | 1988-03-16 | Trisilahydrocarbon lubricants |
Publications (1)
Publication Number | Publication Date |
---|---|
US4788312A true US4788312A (en) | 1988-11-29 |
Family
ID=22614714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/169,225 Expired - Fee Related US4788312A (en) | 1988-03-16 | 1988-03-16 | Trisilahydrocarbon lubricants |
Country Status (1)
Country | Link |
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US (1) | US4788312A (en) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4932976A (en) * | 1989-05-30 | 1990-06-12 | Ethyl Corporation | Textile lubrication |
US5026893A (en) * | 1990-06-11 | 1991-06-25 | Lubricating Specialties Company | Polysilahydrocarbon lubricants |
US5332849A (en) * | 1994-01-03 | 1994-07-26 | Korea Institute Of Science And Technology | Tris(silyl) alkanes and their preparation methods |
US5399740A (en) * | 1993-12-10 | 1995-03-21 | Korea Institute Of Science And Technology | Tris(silyl)methanes and their preparation methods |
US5519157A (en) * | 1994-06-22 | 1996-05-21 | Dow Corning Toray Silicone Co., Ltd. | Fluorine-containing organosilicon compounds and method for their preparation |
US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
US6887835B1 (en) * | 2002-07-09 | 2005-05-03 | Crompton Corporation | Silane additives for lubricants and fuels |
WO2014182681A1 (en) | 2013-05-06 | 2014-11-13 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
US9381506B2 (en) | 2013-11-19 | 2016-07-05 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
US9381505B2 (en) | 2013-11-19 | 2016-07-05 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
US9387468B2 (en) | 2013-11-19 | 2016-07-12 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
US9440999B2 (en) | 2013-05-15 | 2016-09-13 | Momentive Performance Materials Inc. | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
US9447125B2 (en) | 2012-08-16 | 2016-09-20 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
US9890182B2 (en) | 2013-05-06 | 2018-02-13 | Momentive Performance Materials Inc. | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts |
CN114456868A (en) * | 2020-10-21 | 2022-05-10 | 中国石油化工股份有限公司 | Lubricating grease and preparation method thereof |
CN114456867A (en) * | 2020-10-21 | 2022-05-10 | 中国石油化工股份有限公司 | Lubricating grease and preparation method thereof |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2632013A (en) * | 1946-10-09 | 1953-03-17 | Union Carbide & Carbon Corp | Process of producing organosilicon compounds |
US2637738A (en) * | 1949-09-17 | 1953-05-05 | Union Carbide & Carbon Corp | Reaction of silanes with aliphatic unsaturated compounds |
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Cited By (22)
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US4932976A (en) * | 1989-05-30 | 1990-06-12 | Ethyl Corporation | Textile lubrication |
EP0400618A2 (en) * | 1989-05-30 | 1990-12-05 | Ethyl Corporation | Textile lubrication |
EP0400618A3 (en) * | 1989-05-30 | 1991-03-20 | Ethyl Corporation | Textile lubrication |
US5026893A (en) * | 1990-06-11 | 1991-06-25 | Lubricating Specialties Company | Polysilahydrocarbon lubricants |
US5399740A (en) * | 1993-12-10 | 1995-03-21 | Korea Institute Of Science And Technology | Tris(silyl)methanes and their preparation methods |
US5332849A (en) * | 1994-01-03 | 1994-07-26 | Korea Institute Of Science And Technology | Tris(silyl) alkanes and their preparation methods |
US5519157A (en) * | 1994-06-22 | 1996-05-21 | Dow Corning Toray Silicone Co., Ltd. | Fluorine-containing organosilicon compounds and method for their preparation |
US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
US6887835B1 (en) * | 2002-07-09 | 2005-05-03 | Crompton Corporation | Silane additives for lubricants and fuels |
US11052383B2 (en) | 2011-12-14 | 2021-07-06 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
US9447125B2 (en) | 2012-08-16 | 2016-09-20 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
US9371339B2 (en) | 2013-05-06 | 2016-06-21 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
US9890182B2 (en) | 2013-05-06 | 2018-02-13 | Momentive Performance Materials Inc. | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts |
WO2014182681A1 (en) | 2013-05-06 | 2014-11-13 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
US9440999B2 (en) | 2013-05-15 | 2016-09-13 | Momentive Performance Materials Inc. | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
US9387468B2 (en) | 2013-11-19 | 2016-07-12 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
US9381505B2 (en) | 2013-11-19 | 2016-07-05 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
US9381506B2 (en) | 2013-11-19 | 2016-07-05 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
CN114456868A (en) * | 2020-10-21 | 2022-05-10 | 中国石油化工股份有限公司 | Lubricating grease and preparation method thereof |
CN114456867A (en) * | 2020-10-21 | 2022-05-10 | 中国石油化工股份有限公司 | Lubricating grease and preparation method thereof |
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